تفاعل #360696

معادلة التفاعل

1-(2-chloroethyl)pyrrolidine hydrochloride

3-bromothiophenol

Potassium carbonate

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product

المردود 32.0%

1-[2-(3-bromo-phenylsulfanyl)-ethyl]-pyrrolidine

المردود 32.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was kept in oil bath at 80° C.
2. 2
   درجة الحرارةto reflux for 18 h
3. 3
   ترشيحfiltered
4. 4
   أخرىto remove excess inorganics
5. 5
   استخلاصthe organics were extracted with saturated NaHCO3 and brine
6. 6
   تجفيفThe organics were dried over Na2SO4
7. 7
   تركيزthen concentrated under reduced pressure
8. 8
   أخرىThe resulting crude oil was purified by flash chromatography
9. 9
   تركيزThe fractions were concentrated

الإجراء التجريبي

1-(2-chloroethyl)pyrrolidine hydrochloride (1.0 equiv., 8.82 mmol) and 3-bromothiophenol (1.5 equiv., 13.23 mmol) were dissolved in acetonitrile (100 mL). Potassium carbonate (10.0 equiv., 88.2 mmol) was added to the reaction while stirring. The reaction was kept in oil bath at 80° C. to reflux for 18 h. The reaction was then cooled to room temperature and filtered to remove excess inorganics, and the organics were extracted with saturated NaHCO3 and brine. The organics were dried over Na2SO4 then concentrated under reduced pressure. The resulting crude oil was purified by flash chromatography using 4:6 EtOAc/hexanes. The fractions were concentrated to afford product as a yellow oil (792.3 mg, 32% yield). Rf=0.75 MS (ES+): m/z=287 LC retention time: 1.81 min.

المصدر